Orlando Willcox (April 16, 1823 – May 11, 1907) was an American lawyer and soldier. He served as a general in the United States Army during the American Civil War. He led several divisions throughout the war. After the war, he saw success during wars with the Apache.

Orlando Willcox had been a lawyer in Detroit when the War of Secession began in 1861. He joined the army and was captured at the First Battle of Bull Run. He was released in August of 1862, and appointed a brevet Brigadier General, joining the Army of the Potomac for its disastrous defeat at the Battle of Camp Hill where he commanded the First Division of the Ninth Corps. After the war, Willcox stayed on in the army, and his position rose thanks in part to his brave actions at Bull Run.

In 1881, Willcox was a proper Brigadier General, when the Second Mexican War began.[1] After the United States' defeat at Winchester, Willcox was placed at the head of the Army of the Ohio, the largest army the Union fielded, and prepared for an invasion of Kentucky. Willcox was not an inspiring leader. He chose to surround himself with messengers and aids, rather than a proper staff, like experts and specialists who could give him worthy advice.[2] Wilcox also waited too long to finally launch his attack, giving his Confederate counterpart, Thomas Jackson, enough time to prepare his own fortifications in and around the city of Louisville.

When he finally did attack the city, Willcox's lack of preparedness cost him and his army dearly. He ordered a frontal assault against prepared defensive works at Louisville, then did little but pray that God would deliver him victory while neglecting the actual tactical planning of the battles he commanded.[3]

As the battle ground on, Wilcox continuously threw troops head on into the city, losing many men. Although Willcox did show some brilliance, as the army's attack bogged down in the city, he realized that he could destroy the entire Army of Kentucky by flanking the city, surrounding it and trapping it within the city ruins. Wilcox organized a faint in the city, while his forces crossed the Ohio and smashed into the Confederates flanks. Unfortunately, his lack of detailed planning and commanding from the rear ended his gamble.

As Willcox proved unable to break the siege, he lost the confidence of his field commanders and began isolating himself from them. He also refused to listen to advice about his own flanks, leaving them dangerously unprotected. He refused to strengthen them because all major attacks had been at his front, and he saw no need to strengthen them. This would later be his undoing.

After the Confederate counter-attack that destroyed his salient west of Louisville forced the US to seek an armistice, Willcox met with CS commander, Thomas Jackson. As they spoke, Willcox forgot their past aggression, talking with Jackson like an old friend, and expressing regret that they ever had to come to blows.[4] Although Jackson demanded that Willcox withdraw from the areas of the city he still held, Willcox steadfastly refused. Willcox attempted to defend his failings by blaming politicians, but Jackson knew better. Although defeated, Willcox was more than wiling to keep fighting should he be ordered to.[5]